Identification

PhytoHub ID
PHUB000406
Name
Isobetanin
Systematic Name
Not Available
Synonyms
  • isobetanidin 5-O-beta-glucoside
CAS Number
15121-53-6
Average Mass
550.473
Monoisotopic Mass
550.143488905
Chemical Formula
C24H26N2O13
IUPAC Name
(1E,2S)-1-{2-[(2R,4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1lambda5-indol-1-ylium-2-carboxylate
InChI Key
DHHFDKNIEVKVKS-RYGANQNKSA-N
InChI Identifier
InChI=1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)/t12-,14+,17-,18-,19+,20-,24-/m1/s1
SMILES
OC[C@H]1O[C@@H](OC2=C(O)C=C3C(C[C@@H](C([O-])=O)\[N+]3=C/C=C3\C[C@@H](NC(=C3)C(O)=O)C(O)=O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
Structure

Calculated Properties

Solubility (ALOGPS)
5.00e-01 g/l
LogS (ALOGPS)
-3.08
LogP (ALOGPS)
0.21
Hydrogen Acceptors
14
Hydrogen Donors
8
Rotatable Bond Count
7
Polar Surface Area
249.37999999999997
Refractivity
149.70579999999998
Polarizability
52.475488709427225
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-3.6483953658807287
pKa (strongest acidic)
2.4023261997458794
Number of Rings
4
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
Yes

Taxonomy as Food Phytochemical

Family
N-containing compounds
Class
Alkaloids
Sub-class
Betalains

Taxonomy as Metabolite

Metabolite Family
N-containing compound metabolites
Metabolite Class
Alkaloid metabolites
Metabolite Sub-class
Betalains (parent, host and microbial metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
IsobetaninN-containing compoundsAlkaloidsBetalainsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Betalains
Super-class
Alkaloids and derivatives
Sub-class
Betacyanins and derivatives
Direct Parent Name
Betacyanins and derivatives
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "Acetals", "Amino acids", "Azacyclic compounds", "Carbonyl compounds", "Carboxylic acid salts", "Carboxylic acids", "D-alpha-amino acids", "Dialkylamines", "Enamines", "Hexoses", "Hydrocarbon derivatives", "Indolecarboxylic acids", "L-alpha-amino acids", "O-glycosyl compounds", "Organic oxides", "Organic salts", "Organic zwitterions", "Organopnictogen compounds", "Oxacyclic compounds", "Oxanes", "Phenolic glycosides", "Polyols", "Primary alcohols", "Propargyl-type 1,3-dipolar organic compounds", "Secondary alcohols", "Shiff bases", "Tetrahydropyridines", "Tricarboxylic acids and derivatives"]
External Descriptor Annotations
["Betacyanins", "betalain", "glycoside"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "Acetal", "Alcohol", "Alpha-amino acid", "Alpha-amino acid or derivatives", "Amine", "Amino acid", "Amino acid or derivatives", "Aromatic heteropolycyclic compound", "Azacycle", "Benzenoid", "Betacyanin", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid salt", "D-alpha-amino acid", "Enamine", "Glycosyl compound", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydropyridine", "Indole or derivatives", "Indolecarboxylic acid", "Indolecarboxylic acid derivative", "L-alpha-amino acid", "Monosaccharide", "O-glycosyl compound", "Organic 1,3-dipolar compound", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organic salt", "Organic zwitterion", "Organoheterocyclic compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Oxacycle", "Oxane", "Phenolic glycoside", "Polyol", "Primary alcohol", "Propargyl-type 1,3-dipolar organic compound", "Secondary alcohol", "Secondary aliphatic amine", "Secondary amine", "Shiff base", "Tetrahydropyridine", "Tricarboxylic acid or derivatives"]

Spectra from Online Resources

No spectra information available

Food Sources

NameGroup
Prickly pearFruit, Tropical fruits PublicationsShow
Swiss chardVegetables, Leaf vegetables PublicationsShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
IsobetaninPrickly pearFruit, Tropical fruits PublicationsShow
IsobetaninSwiss chardVegetables, Leaf vegetables PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Isobetanin Isobetaninhuman ratplasma, urineunchangedNot Available5-20µmol/L<1%C24H26N2O13550.143488905 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Isobetanin IsobetaninAgeNot studied
Isobetanin IsobetaninBmiNot studied
Isobetanin IsobetaninEthnicityNot studied
Isobetanin IsobetaninGenotypeNot studied
Isobetanin IsobetaninHealth_statusNot studied
Isobetanin IsobetaninMicrobiotaNot studied
Isobetanin IsobetaninSexNot studied
Isobetanin IsobetaninSmokingNot studied
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